As a celebrity, Drake has gone out of his way to piss off Chris Brown, which earns him bonus points in my book. Drake’s history with Chris is convoluted. Here’s what I think happened: Chris and Rihanna were doing the on-and-off thing for a few years, and at some point Rihanna also started hooking up with Drake.
Drake really liked Rihanna and wanted her to be his for-real girlfriend. She still had drama (she thrives on drama) with Chris, so she ended up not being Drake’s girlfriend but they still hooked up sometimes and they’re friends. Drake then throws his history with Rihanna in Chris’s face. Fights ensue. Again, that’s just my theory of how everything went down. I bring this up because Drake talks about his feud with Chris in a new interview.